Even before she took up residence in the White House, Jackie Kennedy was fretting about her image and developing what would become her signature style. She was corresponding with designer Oleg Cassini, who was creating jackets and skirts for her. She was working with a personal shopper at the posh New York department store Bergdorf Goodman to find matching accessories. She knew the eyes of the nation would be scrutinizing her, and she was fortifying her closet in preparation for the spotlight.

Her meticulous approach to fashion is revealed in 17 letters that will be auctioned Nov. 23 in Amesbury as part of a three-day auction of Kennedy possessions and related items at John McInnis Auctioneers
. The auction, which begins Nov. 22, is timed to the 50th anniversary of the assassination of John F. Kennedy.

Many of the letters were written to Bergdorf Goodman’s Marita O’Connor, who acted as the first lady’s personal shopper. The letters, which come directly from O’Connor’s family, are part of lots on which bidding is expected to start at $1,000 to $2,000.

“She knew exactly what she wanted,” appraiser Dan Meader said of Kennedy. “To see her own words, her own design of herself . . . to me it marks a monumental change in American fashion. ”

Not only did Kennedy write letters to O’Connor with sketches of the shoes and hats that she needed to complete her outfits, she also tore pictures out of magazines and newspapers and attached swatches from ensembles that Cassini was creating for her. She sent these to O’Connor — or Miss Marita, as she calls her in the letters — to find the ideal accessories.

“You can tell that she is doing it on the fly,” Meader says. “She’d look at the magazine, tear out a page, and write ‘Marita, this is what I’m looking for, this is what I want.’ It’s pretty telling.”

Other items in the auction include shoes and purses belonging to the first lady, along with a blazer and fedora that belonged to JFK. According to Meader, the letters from the first lady reveal several interesting facts about Kennedy and how she saw her style.

For example, Kennedy had a love/hate relationship with her famous hats.

In one letter to O’Connor, she writes “Oh dear, it was so pleasant when I didn’t have to wear hats! They will pauperize me + I still feel absurd in them!” But in another, she writes, “I prefer to deal with you as hats are the most important thing.”

“She didn’t like wearing hats. He didn’t like wearing hats,” Meader said. “But they knew they had to. Otherwise the hat industry may have collapsed. It’s like when Clark Gable didn’t wear an undershirt [in the movie “It Happened One Night”] and sales of undershirts plummeted.”

She was also often asking O’Connor to look into finding berets.

“I just can’t find one big enough — in beige — a softish wool or cashmere material — I just want to wear it in the park when it’s raining and it must be big enough for me to tuck all my hair into — tell Halston sort of a ‘Jules & Jim’ shape but with a brim. . .!”

The letters also reveal that Kennedy was not shy about asking for advice from some of the biggest names in fashion. In one letter she asks O’Connor to consult with legendary editor Diana Vreeland, who was then working at Harper’s Bazaar and later moved to Vogue. It’s the modern-day equivalent of Michelle Obama consulting with Anna Wintour.

Besides hats, gloves, and purses, Kennedy also had very specific ideas about the kind of shoes she was shopping for. In one case she even drew a sketch of the silhouette of her ideal shoe.